تفاعل #602770

معادلة التفاعل

LiOH.H2O

2-mercaptoacetic acid

(2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)piperidine-1,2-dicarboxylate

→

(2S,5R)-1-tert-butyl 2-ethyl 5-((benzyloxy)amino)piperidine-1,2-dicarboxylate

المردود 85.0%

المذيبات

DMF

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with EtOAc (3×)
2. 2
   غسيلThe combined organic layer was washed with brine (3×)
3. 3
   تركيزconcentrated in vacuum
4. 4
   أخرىpurified by silica gel column chromatography (3; 1 petroleum ether/EtOAc)

الإجراء التجريبي

LiOH.H2O (95 g, 2.3 mol) and 2-mercaptoacetic acid (124 g, 1.3 mol) were added to a solution of (2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)piperidine-1,2-dicarboxylate (251 g, 0.45 mol) in DMF (1200 mL). The reaction mixture was then stirred at 20° C. overnight. The reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organic layer was washed with brine (3×), concentrated in vacuum and purified by silica gel column chromatography (3; 1 petroleum ether/EtOAc) to afford (2S,5R)-1-tert-butyl 2-ethyl 5-((benzyloxy)amino)piperidine-1,2-dicarboxylate (122.9 g, 85%) as a yellow solid.

المصدر